Reactivity in nucleophilic substitution. Part III. The acetolysis of 9-fluorenyl toluene-p-sulphonate

Abstract

The kinetics of acetolysis of 9-fluorenyl toluene-p-sulphonate have been studied. It is shown that the reaction is of the S_N1 type, and linear, normal salt effects are observed on addition of lithium perchlorate. Added common ion, in the form of toluene-p-sulphonic acid, does not depress the rate and there was no maximum in the titrimetric rate coefficient with addition of acetic anhydride to the system. It is concluded that acetolysis occurs to the exclusion of return from free ions, and from intermediates other than intimate ion-pairs.